


10 Things I Loathe About You

by MesserMessa07



Category: Supernatural
Genre: Alternate Universe - High School, Based on the movie, M/M, Sassy Castiel, Some mentions of abuse
Language: English
Status: In-Progress
Published: 2013-01-05
Updated: 2013-01-05
Packaged: 2017-11-23 19:42:18
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,993
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/625839
Author URL: https://archiveofourown.org/users/MesserMessa07/pseuds/MesserMessa07
Summary: <blockquote class="userstuff">
              <p>Sam wants Gabriel, who can't date until his outcast older brother Castiel does. Now it's Dean's job to find his way into Cas' guarded heart, and perhaps truly fall in love on the way.  Based on the movie '10 Things I Hate About You'</p>
            </blockquote>





	10 Things I Loathe About You

**Author's Note:**

> This is also available on fanfiction but that site has been weird for a while now so I'm posting it here as well with corrections and such. I don't own SPN or 10TIHAY obviously. Reviews are very much appreciated!

High school

Sam looked around, taking in the high school scene and sincerely wishing he would find his place in it soon.

His father was constantly switching jobs but after moving to Kansas he promised his only son that they would both settle down. He even opened up his new auto mechanic shop just to prove how serious he was about staying this time. Sam felt both relieved and wary at this unexpected move, just praying it would stick.

Someone tapped his shoulder from behind, nearly scaring him out of his own skin.

"Crap dude," he said, whirling his large frame around to see who was so willing to talk to the new kid.

"Sorry," the boy said, tilting his head up slightly to look at Sam in the face. Since his growth spurt seven months ago, Sam hadn't stopped growing and was nearing the six-foot marker with no signs of stopping. He remembered the days of being scrawny with a grimace and was set on bulking up as much as possible. His Dad's defence lessons could only do so much anyways…

The boy scratched the stubble at his jaw and held out his hand, "My name's Chuck Shirley. I'm supposed to be your guide for the next couple of days."

"Sam Winchester," he said, shaking Chuck's hand and feeling a wave of relief crash over him. "God, I was worried they'd be sending me some art geek or something."

His guide gave a nervous laugh, "Geek? Heh, no geek here. Nope. Now come on, I'll show you around."

The two of them meandered their way through the throngs of kids, Sam trying and probably failing to keep up with all of the two second introductions and instructions Chuck was throwing his way.

"Jo over there's pretty cool but get in trouble with her and you're dead. Her mother's the principle and freaking terrifying…"

"Andy and Ava can't get their hands off each other, like rabbits trying to breed really…"

"Ash is the genius…"

"The brunette over there is Ruby. She's constantly getting high, so unless you want to get addicted to something-"

"Wait, wait!" Sam said, having caught sight of something interesting. "Who's  _that_  guy?"

Chuck followed his gaze, sighed and shook his head. "That's Gabriel Novak, trickster extraordinaire and one big pain in the ass. You swinging for the other team dude?"

Sam cleared his throat, searching for a way out of the uncomfortable question. The last time he'd been open about his sexuality, it hadn't exactly gone well. Then again, if he ever wanted to know more about the lithe trickster he'd better just be straight about it.

"Yup."

Chuck nodded, "That's cool, tons of out people here.... but you're out of your league there."

Sam's hope, which had just soared, suddenly felt crushed. "Why?" he asked, squinting in the afternoon light to get a better look at Gabriel Novak's shiny brown hair and mischievous smile.

"Three reasons," his guide said, marking each rationale with a finger. "One: He's a trickster at heart and doesn't take anything seriously. Two: None of the Novak's can date. Their family is like super religious or something. And three: There's a dick named Crowley who's after him."

The Winchester huffed in annoyance, his frustrations only pacified when his gaze settled once more on the object of his affections. How could he not try to get a guy like that?

Just as he was admiring the other student's body again, Gabriel's eyes flashed his way. His golden orbs settled on Sam's more muted brown ones and the two boys exchanged smiles. Well his was a smile; Gabriel's was more of a curious smirk. Sam made a motion to walk over when Chuck grabbed his arm.

"Hey!" he exclaimed, glaring at his only friend. In response, his guide only motioned over to where Gabriel stood now talking to another boy.

Sam took in the mysterious man's impeccable, black suit and did not like him at all. "Who's that?" he growled, bristling when Gabriel responded to the suit's obvious flirting.

"That is the afore mentioned dick Crowley," Chuck said, his own scowl set firmly in place. "He practically runs the school just 'cause he's got a couple of modelling gigs."

Sam shook his head; "I think I hate the guy already."

"You wouldn't be the first or the last my friend," his guide said, shrugging his shoulders. "Word to the wise though, there are plenty of people who love him too. He's rich, good looking and bi, which for him means he's basically ready to go hump any living thing in sight."

Sam sincerely hoped that Gabriel could see through whatever game Crowley was playing but judging by their flirty conversation, that wasn't happening.

The six-foot goliath was only just barely paying attention to Chuck's continued quick fire introductions as most of his focus was still trained on Gabriel's laughing figure. Crowley was still trying to talk him up and the sight ignited a fire down in his belly. Before he could further dwell on his hatred towards the teenager or his suit, Chuck was leading him over to another section filled with picnic tables.

As they neared one of crowded benches, Sam's guide seemed to straighten up and made a show of the flashy smile he had on his face.

"Ladies. Gentleman," Chuck said, nodding towards a group of students a year or two younger than themselves.

Their eyes flashed and the ringleader ground out, "bite me."

Sam quirked his eyebrow at his friend, "fans of yours?"

"I was their god yesterday," he huffed, "Just because I sent Darren to hell they're all angry. Well they wouldn't know creative genius if it went and bit them on their asses. And another thing-"

Deciding it best to intervene now, Sam cut across and asked, "Wait what? Who did you send to hell?"

"Darren," he explained, still shooting annoyed glares at the group. "He's a character of mine in this graphic novel I created. The school's publishing it but it's not really a big seller…"

"Hey that's pretty cool actually. What's it about?"

Chuck levelled a searching gaze on Sam, judging his tone before answering. "Two brothers on the road hunting monsters. You actually remind me of one of them…"

"Is it the one that went to hell?" he asked.

He laughed and shook his head. "No, the other one, Steve. He's enormous too."

Sam cuffed the writer's head, grinning. "Just means I'm well equipped."

"Yeah well, go and tell Gabe over there about your equipment," Chuck drawled, a slight smirk on his lips. "I'd love to see that conversation."

He rolled his eyes, gaze unconsciously darting back to the trickster. "I'll get to know him, just you wait and see."

His guide snorted again but conceded, "Well I hear he's looking for a French tutor."

"Seriously? Well that's perfect!"

Chuck raised his eyebrows in surprise, "Really, you speak French?"

"No," Sam said, not sounding the lease bit concerned at his lack of linguistic skills. "But I will."

His newfound friend could only sigh and shake his head. Sam was smitten and determined, which was probably not a good combination but perhaps an interesting one at least.

Chuck cleared his straying thoughts and eased himself into a comfortable conversation with Sam as they walked around the school.

Who knew, this might end up making a good story in the end.

* * *

Inside the school, Dean Smith had once again been sent to the school's erratic councillor Ms. Becky. He had never really liked her much, greatly disliking her greedy eyes as she drank the sight of him in. Still, he could usually bull through their encounters and simultaneously hide his discomfort

Yet despite this, it only took a few seconds to begin regretting the actions that had landed him in the room in the first place.

"…And as he slid his hands up the other mans strong, muscular abdomen, he trembled in a desire he knew to be so very wrong…" she whispered to herself, eyes closed as she typed away on her laptop.

"Shall I dim the lights," he joked, having no desire to listen further to her novel or fan fiction or whatever as his eyes darting around the room for an escape.

Her gaze landed on him with startling intensity and he shifted awkwardly from side to side. "Dean," she said finally. "Here to see me again."

"Only so we can share these moments together."

Miss Becky hummed, "I heard you expose yourself in the cafeteria today."

He sighed, recalling the incident. "I was fooling around with the lunch lady with the bratwurst."

"Ah, aren't we the optimist," she said with a sickly sweet smile, giving a rather pointed look at his private region. "Next time, keep it in the pouch."

Dean made a face, not at all enjoying the innuendos she was introducing. Usually he was the one with some sort of obscene comment up his sleeve and he most certainly did not enjoy being on the receiving end. Was this what girls called 'objectifying?'

Shrugging it off, he left the office and just wandered the halls. School had already been let out and most people were milling around outside, enjoying the warming weather. Dean was content to traverse the deserted corridors in the meantime.

* * *

After school now, Chuck led his charge towards the parking lot, although the giant was a little distracted by a certain mischievous trouble maker.

"Don't play it too cool dude," the writer smirked, "he might not realize you like him."

The jab and Sam's blatantly adoring look that he kept sending Gabriel was actually met by a halfway sheepish expression. "I can't help it, he's just so perfect."

"If you by perfect you mean shallow and self-absorbed, then yes, you could consider him perfect."

"No."

"Yes."

"No! You're wrong about him! He's deeper than that," Sam insisted, his eyes never leaving the tricksters form as he walked several metres in front of the duo.

Chuck rolled his eyes, fully knowing his friend was a lost cause. "Just calling them as a see 'em."

Sam just continued to shake his head in defiance. 

As they neared the teeming lot, the enthralled boy had to watch with sad eyes as his new crush accepted a ride from his now most hated enemy... Crowley Donner.

The writer patted the giants shoulder as he strapped on his helmet, standing beside his small electric scooter. "No worries dude, he'll forget all about Crowley Donner in no time."

Sam nodded without conviction, standing aside as his friend mounted the scooter, sidling out of the parking spot.

Suddenly a car came rushing forward, honking loudly at the unexpected roadblock in their path.

"Could you move that damn contraption please," the driver shouted with an oddly polite edge, car horn blaring in annoyance. Chuck lifted his hand in apology and almost toppled over with the loss of balance. Obviously deciding his best chance of  _not_  being run over was to just move out of the way, he jerked his small bike forwards.

The elderly car quickly rolled past and snaked out of the parking lot.

"You OK there?" Sam asked, having torn his eyes away from Gabriel retreating form long enough to take in the scene.

Chuck nodded, "Just a minor run in with the shrew. That's your love's brother, Castiel Novak, you know."

"What Gabriel's?" Sam asked in shock, not at all able to believe his sweet crush could possibly have such an irritable relation.

"Yup, so looking forward to the family dinners yet?" he asked with a wry smile.

Sam shoved him lightly and waved goodbye, finally deciding to head home now that Gabriel was gone.

* * *

Sprawled across his couch, Castiel Novak was feeling particularly content as he read through the monstrous tome  _War and Peace._ He was what most described as an odd boy. Up until a couple of years ago, Castiel had been the perfect son and brother to his family; he got good grades and followed orders to the letter. Since then however, he'd begun to rebel against both his family and society. So it really wasn't an unusual thing for his eldest brother Michael to come storming into the living room, anger and confusion lining his face

"What is this?" he asked, his voice struggling to remain even.

Castiel glanced at him, face expressionless. "Well Michael, it looks like an envelope but I suppose you're referring to what's inside the envelope."

His brother was obviously having a difficult time keeping his emotions in check at this point, "It's a letter from Cranbrook-"

"Cranbrook!" Castiel exclaimed, immediately leaping to his feet and snatching the paper out of his hands. He ripped it open and scanned the letter, quickly finding the sentence he was looking for.

"I got in! I got in!" he shouted, practically jumping up and down. Even Michael's crossed arms and scowl wasn't enough to stop Castiel's exuberance.

Raphael Novak entered the room to investigate the commotion his normally quiet and serious brother was creating. "What's going on here?" he asked, surveying the scene with interest.

"I got into Cranbrook!"

The two brothers frowned. "Isn't that that fancy art school in Michigan?" Raphael asked.

Michael added, "I thought we agreed you were going to the community college, become a Husky" with a half hearted fist pump.

"No, you two agreed," Castiel said sighing, his excitement finally fading. "I want to go to Cranbrook."

Raphael crossed his arms, "but it's thousands of miles away."

"Thus the basis of its appeal."

Before the two older brothers could begin their argument again, Gabriel walked into the feud with a lollipop lodged in his mouth. Seeing their scowling expressions, he promptly turned around to walk out again.

"Gabe!" All three brothers called before resuming glaring at one another.

The self-proclaimed trickster sidled into the room, masking his discomfort with one of his trademark grins. "Need anything chuckleheads, or just another target for your frowning competition?"

Judging by the withering glower Castiel sent him alone, Gabriel was pretty certain he'd be dead by now if looks could kill.

Then his face suddenly brightened and glint came to his blue eyes that scared all three of Castiel's brothers more than they cared to admit. Seeing as the maniac shine was currently focussed on Gabriel though, the youngest Novak was certain that his fear outweighed the rest.

"Michael, Raphael. Ask who drove Gabriel home today," Castiel said, a smirk on his dry lips.

His eyes widened in realization and he sent his own glare at his older brother for ratting him out.

"Now don't try to change the subject Cast- wait, drove? Who drove you home?" Michael began before quickly changing his attention to Gabriel, who looked like a deer in the headlights.

He blinked, composed himself and said in his most casual voice, "Nothing to be upset about Mikey, just this boy named Crowley Donner-"

"Who's a jerk," Castiel interjected.

Gabriel scowled at his brother and continued, "and who might actually like me."

"No, no. You know the rules; no dating in high school," Raphael said, shaking his head.

"But Dad hasn't been here forever!"

"Doesn't matter," Michael said, his voice taking on a more serious tone. "He's gone so we're in charge and we stand by his rules."

Gabriel groaned, tired of his families overly religious conduct. "Everyone else is dating!"

"Oh no they aren't. Your brother isn't."

Castiel nodded, "And I don't intend to."

"And why is that?" Michael asked, waiting for one of his favourite responses.

Castiel tilted his head, "Well I don't fully understand the concept of dating. Most of these feelings and urges are simply overactive hormones triggered by our pubescent state. These animalistic desires will start to fade as we begin to mature and at that time we are more able to make an informed decision as to our mate."

"Exactly," Raphael nodded, though he hadn't really listened to whatever oddly worded reason Castiel had come up with this time.

"It's like the Pizza Man," Castiel said, continuing to babble, "If he had truly loved her, then why did he slap her rear?"

All three brother's rolled their eyes at Castiel's musings. They had tried to introduce their more oblivious brother to the concept of porn as a way to avoid having 'the talk' with him. Unfortunately, he hadn't really understood the concept and was fixated on such details and morals. So instead, Michael and Raphael had just bought him a medical book on the process of sex, which led to the textbook answers they were now all doomed to hear from him whenever the topic came up.

"It's an idiotic rule, I can take care of myself," Gabe frowned.

Raphael opened his mouth to protest once more but Michael suddenly cut him off, an idea forming in his head.

"Wait! Old rule out, new rule in." Michael said, smiling. "You can date."

Gabriel grinned while both Castiel and Raphael's mouths dropped.

"When he does," he finished, pointing at Castiel.

"But what if he never dates! He's like some sort of mutant!" Gabriel demanded, chasing after Michael when he left the room.

The older brother grinned, "Then you'll never date. Ooh! I like the sound of that! And we'll talk about Cranbrook later," he added to Castiel.

"Fine," he responded, reclining back on the couch.

Gabriel huffed and turned to the source of his new dilemma. Castiel had maintained a neutral expression throughout most of the conversation, except for a slight, puzzled furrow of the brows.

"Can't you just go on one date? So I can finally have a life!"

Castiel frowned, "but I have no desire to date, I just said so…"

Gabriel let out another frustrated sound, climbing up the stairs to shut himself in his bedroom, unaware just how far someone was willing to go for him to get that one date.

And that person was Sam Winchester.


End file.
